racFTY720 Phosphate Chemical Properties

Melting point:

122-124°C

Boiling point:

584.2±60.0 °C(Predicted)

Density 

1.172±0.06 g/cm3(Predicted)

storage temp. 

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

solubility 

Chloroform : Methanol (Slightly, Heated), Methanol (Slightly, Heated)

pka

1.73±0.10(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

racFTY720 Phosphate Usage And Synthesis

Chemical Properties

White Solid

Uses

Labelled rac FTY720 (F805010). rac FTY720 is a sphingosine 1-phosphate receptor modular, ameliorates experimental autoimmune encephalomyelitis by inhibition of T cell infiltration.

Definition

ChEBI: Fingolimod phosphate is a primary amino compound that is fingolimod in which one on the hydroxy groups has been converted into its dihydrogen phosphate derivative. It is the active metabolite of fingolimod. It has a role as an antineoplastic agent, an immunosuppressive agent and a sphingosine-1-phosphate receptor agonist. It is a monoalkyl phosphate, a primary amino compound and a primary alcohol. It is functionally related to a fingolimod.

Biological Activity

fty720 is sphingosine-1-phosphate (s1p) receptors agonist [1]. fty720 is a novel immunomodulatory agent derived from isp-1 (myriocin), a fungal metabolite that exists in traditional chinese herbal medicine. in higher eukaryotes, s1p is the ligand for five g-protein-coupled receptors. these s1p receptors are differentially expressed and regulate vascular maturation, angiogenesis, cardiac development and immunity. s1p receptors are important for directed cell movement [2].

in vitro

the phosphorylated fty720 acted as agonist for a family of g protein-coupled receptors in vitro. fty720 inhibited sphingosine-1-phosphate lyase activity [3]. fty720 phosphate acted as a potent agonist at sphingosine-1-phosphate (s1p) receptors s1p1, s1p3, s1p4, and s1p5 with ic50 values of 0.2-6 nm [3].

in vivo

in a variety of transplant and autoimmune models, fty720 was efficacious without inducing a generalized immunosuppressed state. fty720 was effective in human kidney transplantation. fty720 elicited lymphopenia resulting from a reversible redistribution of lymphocytes from circulation to secondary lymphoid tissues by unknown mechanisms. in a rodent model of multiple sclerosis, the phosphorylated fty720 compound was a potent agonist at four s s1p receptors. phosphorylation of fty720 acted through sphingosine 1-phosphate signaling pathways to modulate chemotactic responses and lymphocyte trafficking [1]. fty720 was phosphorylated in vivo. in mice, treatment with fty720 inhibited tissue sphingosine-1-phosphate lyase activity, whereas lyase gene and protein expression were not significantly affected [3].

References

[1] brinkmann v, davis m d, heise c e, et al. the immune modulator fty720 targets sphingosine 1-phosphate receptors[j]. journal of biological chemistry, 2002, 277(24): 21453-21457.
[2] spiegel s, milstien s. sphingosine-1-phosphate: an enigmatic signalling lipid[j]. nature reviews molecular cell biology, 2003, 4(5): 397-407.
[3] bandhuvula p, tam y y, oskouian b, et al. the immune modulator fty720 inhibits sphingosine-1-phosphate lyase activity[j]. journal of biological chemistry, 2005, 280(40): 33697-33700.

racFTY720 Phosphate(402615-91-2)Related Product Information

• (S) FTY720 PHOSPHATE
• 1,3-Propanediol, 2-amino-2-[2-(4-decylphenyl)ethyl]-
• 2-NitrodeaMino FingoliMod
• Heptyl Deoctyl Fingolimod Hydrochloride
• N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide
• Fingolimod
• Fingolimod
• Fingolimod Impurity 7
• N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl)butan-2-yl)acetamide
• 2-DiMethylaMino FingoliMod
• Fingolimod
• Fingolimod Impurity 11
• 3-AMino-3-(hydroxyMethyl)-1-(4-octylphenyl)-1,4-butanediol
• Fingolimod
• Fingolimod Hexyl Impurity
• Fingolimod
• Fingolimod
• Fingolimod Stearate Amide